Sodium Hydroxide → HCID 57794814, compound

HRID 2099286Notes

Reaction equation

HRID 2099286 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 57794763HCID 57794763, compound

Product 1

HCID 57794814HCID 57794814, compoundYield 89.6%

Reagents, catalysts & solvents 3

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

Procedure

1,1-dimethylethyl {[(1S,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}methylcarbamate (12.02 g, 41.2 mmol), accessed via the method of Preparation 13A, was dissolved in 200 mL DCM with 6.2 mL 2-methylpropan-2-ol and treated with Dess-Martin Periodinane (28.0 g, 66.0 mmol, 1.6 eq) in 200 mL DCM at ambient temperature for 3 h. The reaction mixture was diluted with 1 L diethyl ether and treated with 400 mL 1N NaOH at ambient temperature for 30 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 with EtOAc/hexanes (1:4)) to give the title compound (10.7, 36.9 mmol, 89%). 1H NMR (400 MHz, CDCl3) δ9.77-9.65 (m, 1H), 7.33-7.23 (m, 5H), 3.75-3.63 (m, 2H), 2.72-2.50 (m, 3H), 2.26-2.19 (m, 1H), 1.87-1.81 (m, 1H), 1.65-1.61 (m, 1H), 1.31-1.18 (m, 9H). 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 with EtOAc/hexanes (1:4))

Sources & evidence

ORD record
ord-5622d2c9aec34f7e9bdf240a6195e080
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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