Sodium Hydroxide → HCID 57794813, compound

HRID 2099287Notes

Reaction equation

HRID 2099287 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@:4]1([CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.CC(O)(C)C.C(OCC)C>[CH:2]([C@@H:3]1[CH2:5][C@:4]1([CH2:12][N:13]([CH3:21])[C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:1]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 57794816HCID 57794816, compound

Product 1

HCID 57794813HCID 57794813, compoundYield 84.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

1,1-dimethylethyl {[(1R,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}methylcarbamate (3.8 g, 13.0 mmol), accessed via the method of Preparation 13B, was dissolved in 35 mL DCM with 1.1 mL 2-methylpropan-2-ol and treated with Dess-Martin Periodinane (8.8 g, 20.8 mmol, 1.6 eq) in 35 mL DCM at ambient temperature for 2 h. The reaction mixture was diluted with 50 mL diethyl ether and treated with 50 mL 1N NaOH at ambient temperature for 15 min. The organic phase was separated, the aqueous phase extracted twice with diethyl ether, the organic phases combined, washed with brine, dried over MgSO4, filtered and concentrated to a colorless oil. The crude material was purified by flash chromatography (SiO2, eluted EtOAc/hexanes (3:7)) to give the title compound (3.2 g, 11.0 mmol, 84%). 1H NMR (400 MHz, CDCl3) δ 8.49-8.47 (m, 1H), 7.29-7.24 (m, 5H), 3.62-3.58 (m, 1H), 3.33-3.22 (m, 1H), 2.72-2.58 (m, 3H), 1.84-1.81 (m, 1H), 1.71-1.53 (m, 1H), 1.34-1.25 (m, 10H). ES-LCMS m/z 312.2 (M+Na).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase extracted twice with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a colorless oil
  7. customThe crude material was purified by flash chromatography (SiO2, eluted EtOAc/hexanes (3:7))

Sources & evidence

ORD record
ord-52a6311506e742708761c0a05d7b0d6d
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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