Benzyl chloroformate → HCID 66936034, compound

HRID 1366500Notes

Reaction equation

HRID 1366500 reaction equation
Cl.[CH3:2][C:3]1([CH3:9])[CH2:7][NH:6][CH2:5][C@@H:4]1[OH:8].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C(Cl)Cl>[OH:8][C@H:4]1[CH2:5][N:6]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][C:3]1([CH3:9])[CH3:2]

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 66936199(R)-4,4-Dimethylpyrrolidin-3-ol hydrochloride

Product 1

HCID 66936034HCID 66936034, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (3R)-4,4-dimethyl-3-pyrrolidinol hydrochloride (0.9920 g, 6.630 mmol) in 1:1 DCM-1 N aq. NaOH (33 mL) was added benzyl chloroformate (0.994 mL, 6.963 mmol). The mixture was vigorously stirred overnight and then diluted with DCM (100 mL). The phases were partitioned, and the organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was then purified by silica gel chromatography (40% EtOAc in hexanes) to afford phenylmethyl (4R)-4-hydroxy-3,3-dimethyl-1-pyrrolidinecarboxylate (1.4654 g, 89% yield) as a colorless oil. LCMS: (M+H)+: 250.1.

Workup

  1. customThe phases were partitioned
  2. dry with materialthe organic phase was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by silica gel chromatography (40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3612d58a275a44bcbc114dcd38a863c7
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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