Triethylamine → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

HRID 346466Notes

Reaction equation

HRID 346466 reaction equation
C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.N1CCC[C@H]1CO.C(N(CC)CC)C.[C:30]([N:37]1[CH2:43][CH2:42][CH2:41][C@H:38]1[CH2:39][OH:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>ClCCl>[C:30]([N:37]1[CH2:43][CH2:42][CH2:41][C@H:38]1[CH:39]=[O:40])([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 640091L-ProlinolHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 31.4 g (144 mmol) di-tert-butyl dicarbonate in dichloromethane was added to a solution of 14.6 g (144 mmol) L-prolinol and 22.1 ml (159 mmol) triethyl amine in dichloromethane at 0° C. The reaction was left overnight at rt. The dichloromethane phase was washed with 30% citric acid aq, saturated NaCl aq and saturated NaHCO3 aq. The organic phase was dried with Na2SO4 and evaporated. Yield 27.71 g (138 mmol, 96%). 27.71 g (138 mmol) BOC-L-prolinol was oxidized to the corresponding aldehyde according to procedure G. Yield of crude product 22.63 g. The product was purified with a silica column using 20% ethyl acetate in petroleum ether as eluent. Yield 18.4 g (92 mmol, 67%).

Workup

  1. washThe dichloromethane phase was washed with 30% citric acid aq, saturated NaCl aq and saturated NaHCO3 aq. The organic phase
  2. dry with materialwas dried with Na2SO4
  3. customevaporated
  4. customThe product was purified with a silica column

Sources & evidence

ORD record
ord-cd2d4469c1564c149af4bb0699e90832
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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