Dimethyl Sulfoxide → tert-butyl N-((1-formylcyclopentyl)methyl)carbamate

HRID 1426645Notes

Reaction equation

HRID 1426645 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:26])[NH:17][CH2:18][C:19]1([CH2:24][OH:25])[CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:14])([CH3:13])[CH3:12].O>C(Cl)Cl>[C:11]([O:15][C:16](=[O:26])[NH:17][CH2:18][C:19]1([CH:24]=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]1)([CH3:12])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 57478044tert-butyl N-{[1-(hydroxymethyl)cyclopentyl]methyl}carbamate

Product 1

HCID 57480691tert-butyl N-((1-formylcyclopentyl)methyl)carbamateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (456 mL, 5.38 mmol) in DCM (30.0 mL) at −78° C. was added DMSO (637 mL, 8.97 mmol) and the resulting mixture was stirred for 5 minutes. tert-Butyl[1-(hydroxymethyl)cyclopentyl]methylcarbamate (1.03 g, 4.48 mmol) in DCM (10.0 mL) was added and the resulting mixture was stirred for 30 minutes at −78° C. TEA (2.50 mL, 17.9 mmol) was added and the resulting mixture was allowed to warm to ambient temperature over 30 minutes. Water was added. The organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine, and then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (957 mg, 94%). 1H NMR (300 MHz, CDCl3): δ 9.39 (s, 1H), 4.94 (br s, 1H), 3.25 (d, 2H), 1.89-1.46 (m, 8H), 1.41 (s, 9H).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes at −78° C
  2. washThe organic phase was washed sequentially with 0.1 N HCl, water, saturated sodium bicarbonate solution, and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8f43301c6b834a2aad35dfb454c9d9df
Source dataset
uspto-grants-2015_01
Patent number
US08933086B2

Reaction notes

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