Dichloromethane → HCID 67062250, compound

HRID 337665Notes

Reaction equation

HRID 337665 reaction equation
ClCCl.[C:4]([O:8][C:9](=[O:32])[N:10]([CH2:14][C:15]1[CH:20]=[C:19]([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[OH:22])[C:18]([CH3:30])=[C:17]([Br:31])[CH:16]=1)[CH:11]1[CH2:13][CH2:12]1)([CH3:7])([CH3:6])[CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>CCOCC>[C:4]([O:8][C:9](=[O:32])[N:10]([CH2:14][C:15]1[CH:20]=[C:19]([C:21](=[O:22])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[C:18]([CH3:30])=[C:17]([Br:31])[CH:16]=1)[CH:11]1[CH2:13][CH2:12]1)([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 66896396HCID 66896396, compound

Product 1

HCID 67062250HCID 67062250, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a dichloromethane (0.1 M) solution of tert-butyl{3-bromo-5-[(3-fluorophenyl)(hydroxyl)methyl]-4-methylbenzyl}cyclopropylcarbamate (1 eq.) from the previous step was added Dess-Martin periodinane (1.0 eq.) and sodium bicarbonate (1.2 eq.). After stirring at RT for 1 h, the reaction mixture was diluted with ether and washed sequentially with sat. aq. NaHSO3, 1 N aq. NaOH, water and brine. The organic extract was dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the title compound as a colorless oil.

Workup

  1. washwashed sequentially with sat. aq. NaHSO3, 1 N aq. NaOH, water and brine
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-b17f86667cd649c5b19580cb08298b45
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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