Acetic Anhydride → Methyl(2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

HRID 884035Notes

Reaction equation

[C:1]([N:8]1[CH2:12][C@@H:11]([NH:13][CH:14]2[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:22]([O:24][CH3:25])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:26][C:27](OC(C)=O)=[O:28]>N1C=CC=CC=1>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([C:27](=[O:28])[CH3:26])[CH:14]2[CH2:19][CH2:18][C:17]([CH3:20])([CH3:21])[CH2:16][CH2:15]2)[CH2:10][C@H:9]1[C:22]([O:24][CH3:25])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

Methyl (2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate (1.01 g, 2.84 mmol) obtained in Step A, was dissolved in pyridine (5 mL), and Ac2O (1.34 mL, 14.20 mmol) was added thereto at room temperature. The reaction solution was heated to 90° C. and was stirred for 2 hours. After the reaction was completed, CuSO4.5H2O aqueous solution was added and the solution was extracted with EtOAc. The extracted organic solution was dried over MgSO4 and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent: EtOAc/Hex=1/1) to give the title compound (0.98 g, 87%).

Workup

customat room temperature
extractionthe solution was extracted with EtOAc
dry with materialThe extracted organic solution was dried over MgSO4
concentrationconcentrated in vacuo
customThe obtained residue was purified by column chromatography (eluent: EtOAc/Hex=1/1)

Sources & evidence

ORD record: ord-50e375d234234814983976c2f63583d3
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236955B2

Reaction notes

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