Methyl chloroformate → HCID 66662384, compound

HRID 969190Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@@H:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@H:15]([C:24](O)=[O:25])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OC)=O.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:13]3[CH2:17][C@@H:16]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C@H:15]([CH2:24][OH:25])[CH2:14]3)=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of (3S,4R)-1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-4-phenylpyrrolidine-3-carboxylic acid (80 mg, 0.0002 mol, example 355) in tetrahydrofuran (2 mL, 0.02 mol) were added triethylamine (0.0316 mL, 0.000227 mol) and methyl chloroformate (20.0 μL, 0.000260 mol) at −15° C. The mixture was stirred at −15° C. for 20 minutes. To the above mixture was added sodium borohydride (16.4 mg, 0.000433 mol) in THF and the resulting mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched by water and then was extracted with AcOEt. The organic layer was dryed over MgSO4, and concentrated to afford the product. The product was purified with Combiflash eluting with 60% AcOEt in hexanes. LCMS: m/z 356.4 (M+H)+

Workup

stirringthe resulting mixture was stirred at 0° C. for 1 h
customThe reaction mixture was quenched by water
extractionwas extracted with AcOEt
concentrationconcentrated
customto afford the product
customThe product was purified with Combiflash
washeluting with 60% AcOEt in hexanes

Sources & evidence

ORD record: ord-5d54ec3f1dbe404fb0bb471fdffd8418
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304081B2

Reaction notes

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