Benzyl chloroformate → Phenylmethyl (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinecarboxylate

HRID 548939Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl.O>[C:9]([O:8][C:7]([NH:6][C@@H:3]1[CH2:4][CH2:5][N:1]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:2]1)=[O:13])([CH3:10])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-Butyl (3S)-pyrrolidin-3-ylcarbamate (10.0 g, 53.7 mmol) in DCM (40 ml) was treated with TEA (14.9ml, 107 mmol) and cooled to 0° C. Benzyl chloroformate (7.6 ml, 53.7 mmol) was added dropwise and the resulting suspension was allowed to warm gradually to room temperature over a period of 18 hours. The reaction mixture was diluted with water (100 ml) and the organic phase separated. The aqueous phase was extracted with further DCM (2×50 ml) and the combined organic extracts dried (sodium sulphate) and concentrated in vacuo to give a pale yellow solid (14.6 g, 85%)

Workup

temperatureto warm gradually to room temperature over a period of 18 hours
customthe organic phase separated
extractionThe aqueous phase was extracted with further DCM (2×50 ml)
dry with materialthe combined organic extracts dried (sodium sulphate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7aa28768b5b04cd4acb567739fbb9cdc
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943628B2

Reaction notes

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