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

HRID 45046Notes

Reaction equation

HRID 45046 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(Cl)Cl>[CH:12]([C:13]1([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:11]

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 μL, 5.38 mmol) in DCM (30.0 mL) at −78° C. was added DMSO (637 μL, 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-1a149f56c8944f50b6f9c9eaab8e57b3
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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