Sodium Sulfite → HCID 57659757, compound

HRID 1011612Notes

Reaction equation

HRID 1011612 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH:14]([OH:15])[CH2:13][C@@H:12]([CH:16]2[CH2:18][CH2:17]2)[N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]1[C:14](=[O:15])[CH2:13][C@@H:12]([CH:16]2[CH2:17][CH2:18]2)[N:11]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 57659765HCID 57659765, compound

Product 1

HCID 57659757HCID 57659757, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5S)-tert-Butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-cyclopropyl-3-hydroxypyrrolidine-1-carboxylate (33) (2.72 g, 7.32 mmol) was dissolved in CH2Cl2 (35 mL). NaHCO3 (2.76 g, 32.9 mmol) and Dess-Martin periodinane (4.65 g, 10.98 mmol) were added and the resulting suspension was stirred at rt for 2 h. A mixture of sat. aq. NaHCO3 and sat. aq. sodium sulfite (20 mL, 1/1) was added and the resulting solution was stirred for 15 minutes. The biphasic mixture was extracted with CH2Cl2 (30 mL) and the organic phase was dried (Na2SO4), filtered, concentrated under vacuum and purified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1 to give 1.54 g (56%, 3 steps) of (5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-cyclopropyl-3-oxopyrrolidine-1-carboxylate (34). Retention time (min)=2.628, method [2], MS (m/z) 392.2 (M+Na)+.

Workup

  1. additionwas added
  2. stirringthe resulting solution was stirred for 15 minutes
  3. extractionThe biphasic mixture was extracted with CH2Cl2 (30 mL)
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. custompurified on a silica gel column (eluant hexane/EtOAc, 9/1 to 1/1

Sources & evidence

ORD record
ord-849d723f6b6c4826b1b9d0dd12c10a36
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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