ChemicalBook CAS DataBase List (R)-TERT-BUTYL (5-BROMO-2,3-DIHYDRO-1H-INDEN-1-YL)CARBAMATE

(R)-TERT-BUTYL (5-BROMO-2,3-DIHYDRO-1H-INDEN-1-YL)CARBAMATE synthesis

5synthesis methods

Product Name:(R)-TERT-BUTYL (5-BROMO-2,3-DIHYDRO-1H-INDEN-1-YL)CARBAMATE
CAS Number:903555-98-6
Molecular formula:C14H18BrNO2
Molecular Weight:312.2

24424-99-5 Synthesis

24424-99-5
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(R)-TERT-BUTYL (5-BROMO-2,3-DIHYDRO-1H-INDEN-1-YL)CARBAMATE

903555-98-6
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Yield:903555-98-6 83 %

Reaction Conditions:

with triethylamine in dichloromethane at -5 - 20;

Steps:

7

To a solution of (R)-5-bromo-2,3-dihydro-lH-inden-l-amine (31.8 g, 150 mmol, 1.0 equiv) in CH2CI2 (500 mL) was added TEA (22.7 g, 224.8 mmol, 1.5 equiv) and a solution of (BOC)₂O (39.2 g, 180 mmol, 1.2 equiv) in CH2CI2 (150 mL) dropwise at -5 °C over a period of 45 min. The mixture was then warmed to rt, stirred for 2 h, diluted with CH2CI2 (200 mL), washed with water (500 mL) and brine (200 mL) twice, dried over anhydrous sodium sulfate, and concentrated. The solid was triturated with hexanes (300 mL) to give 38.7 g (83%) of tert- butyl (R)-(5-bromo-2,3-dihydro-lH-inden-l-yl)carbamate as a white solid. LRMS (ES): calculated for CuHisBrNCL, 311.1 Da, measured 256, 258 m/z [M+H-56]⁺.

References:

WO2023/15184,2023,A1 Location in patent:Paragraph 0104