Sodium Sulfite → HCID 68611061, compound

HRID 2095296Notes

Reaction equation

HRID 2095296 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([C@H:20]2[CH2:22][C@@H:21]2[CH2:23]O)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:19]=[N:18][CH:17]=[C:16]([C@H:20]2[CH2:22][C@@H:21]2[CH:23]=[CH2:25])[CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 68613216HCID 68613216, compound

Product 1

HCID 68611061HCID 68611061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1S,2S)-2-[5-[[1-(tert-butoxycarbonyl)-(2S)-azetidinyl]methoxy]-3-pyridyl]cyclopropylmethanol (3.00 g, 8.97 mmol) in CH2Cl2 (25 mL) was treated with 3 equiv. of NaHCO3 followed by Dess-Martin periodinane (7.60 g, 18.0 mmol, 2.0 equiv.). The solution was stirred for 2 h at room temperature. Saturated aqueous Na2SO3 (5 mL) and NaHCO3 (5 mL) were then added, and the biphasic mixture was stirred for 15 min and extracted with EtOAc (2×100 mL). The organic phase was washed with brine (50 mL), dried (Na2SO4), and concentrated in vacuo. The resulting aldehyde was purified by CC and directly used in the next reaction.

Workup

  1. stirringthe biphasic mixture was stirred for 15 min
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting aldehyde was purified by CC
  7. customdirectly used in the next reaction

Sources & evidence

ORD record
ord-8622cdb6b89e49a3964109022d37b520
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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