Benzyl succinimido carbonate → Benzyl 3,3,3-trifluoro-2-hydroxy-2-methylpropylcarbamate

HRID 444952Notes

Reaction equation

HRID 444952 reaction equation
Cl.[NH2:2][CH2:3][C:4]([CH3:10])([OH:9])[C:5]([F:8])([F:7])[F:6].[C:11](=O)([O:20]N1C(=O)CCC1=O)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.O>[F:6][C:5]([F:8])([F:7])[C:4]([OH:9])([CH3:10])[CH2:3][NH:2][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 717573513-Amino-1,1,1-trifluoro-2-methylpropan-2-ol hydrochloride2×

Product 1

HCID 67383276Benzyl 3,3,3-trifluoro-2-hydroxy-2-methylpropylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of amino-1,1,1-trifluoro-2-methylpropan-2-ol hydrochloride (Intermediate R) (1.5 g, 8.35 mmol) in DCM (50 ml) was added TEA 93.54 g, 35.0 mmol) followed by benzyl 2,5-dioxopyrrolidin-1-yl carbonate (1.983 g, 7.96 mmol). The mixture was stirred at RT for 6 hours and then diluted with water. The organic portion was separated using a phase separator and concentrated in vacuo. Purification by chromatography on silica eluting with 0-70% EtOAc in iso-hexane afforded the title product; 1H NMR (400 MHz, DMSO-d6) δ 7.34 (6H, m), 5.98 (1H, s), 5.05 (2H, s), 3.31 (1H, m), 3.18 (1H, m), 1.21 (3H, s) LC-MS: Rt 1.05 min; MS m/z 278.1 [M+H]+; Method 2 minLC_v003.

Workup

  1. customThe organic portion was separated
  2. concentrationconcentrated in vacuo
  3. customPurification by chromatography on silica eluting with 0-70% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-b295bfdd67244b6cad07fecf111e8a1c
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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