Sodium Hydroxide → HCID 57794815, compound

HRID 2099275Notes

Reaction equation

HRID 2099275 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@:4]1([CH2:12][N:13]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[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]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:1]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 57794738HCID 57794738, compound

Product 1

HCID 57794815HCID 57794815, compoundYield 69%

Reagents, catalysts & solvents 3

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

Procedure

N-{[(1R,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide (600 mg, 1.82 mmol), accessed via the method of preparation 7B, was dissolved in 18 mL DCM with 270 uL 2-methylpropan-2-ol and treated with Dess-Martin Periodinane (1.23 g, 2.90 mmol, 1.6 eq) at ambient temperature for 16 h. The reaction mixture was diluted with 42 mL diethyl ether and treated with 22 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 successively with DCM, EtOAc/hexanes (1:4)) to the title product (410 mg, 1.24 mmol, 69%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.54 (d, J=6.7 Hz, 1H), 7.65 (m, 2H), 7.55 (m, 1H), 7.47 (m, 2H), 7.31-7.23 (m, 5H), 3.50 (d, J=14.3 Hz, 1H), 3.09 (d, J=14.3 Hz, 1H), 2.52 (s, 3H), 2.15-2.08 (m, 1H), 1.93 (m, 1H), 1.76-1.73 (m, 1H).

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

Sources & evidence

ORD record
ord-efdf8b6d080740d297ddb2735e41a50a
Source dataset
uspto-grants-2009_08
Patent number
US07569579B2

Reaction notes

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