Sodium Sulfite → (2R,3S,5S)-5-Formyl-3-isopropyl-2-[4-methoxy-3-(3 methoxy-propoxy)-phenyl]pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 500009Notes

Reaction equation

CC1(C)N([O])C(C)(C)CCC1.[C:12]([O:16][C:17]([N:19]1[C@H:23]([CH2:24][OH:25])[CH2:22][C@@H:21]([CH:26]([CH3:28])[CH3:27])[C@@H:20]1[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])O.[Na+].[Br-].[K+].Cl[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>ClCCl.O>[C:12]([O:16][C:17]([N:19]1[C@H:23]([CH:24]=[O:25])[CH2:22][C@@H:21]([CH:26]([CH3:28])[CH3:27])[C@@H:20]1[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH2:38][CH2:39][CH2:40][O:41][CH3:42])[CH:30]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 5 °C

Procedure

Using TEMPO: A mixture of 0.96 g of the alcohol 6, 0.044 g of sodium hydrogencarbonate, 0.026 g of potassium bromide and 0.051 g of TEMPO in 3 mL of dichloromethane and 1.2 mL of water is cooled to 5° C. To the mixture is added dropwise 0.13 g of 10-13% sodium hypochlorite solution, and the mixture stirred for 5 h between 5° C. and 20° C., before addition of 0.57 g of sodium sulfite. The phases are then separated and the organic phase washed twice with 5 mL of water. Evaporation of the solvent in vacuum affords e.g. 0.50 g of the aldehyde 7 as an oil.

Workup

customThe phases are then separated
washthe organic phase washed twice with 5 mL of water
customEvaporation of the solvent in vacuum

Sources & evidence

ORD record: ord-f1f6f48d48664c91810e9abb0d65dd83
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767831B2

Reaction notes

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