Sodium Hydroxide → HCID 69039795, compound

HRID 1454247Notes

Reaction equation

HRID 1454247 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@:9]1([CH:18]=O)[CH2:14][CH2:15][CH:16]=O)([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@:9]21[CH2:18][N:27]([CH2:26][C:25]1[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=1)[CH2:16][CH2:15][CH2:14]2)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 673264-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86600472HCID 86600472, compound

Product 1

HCID 69039795HCID 69039795, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(1R,2S)-2-formyl-2-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (4.73 g, 16.7 mmol) and 4-fluorobenzylamine (2.3 g, 18 mmol) in dichloromethane (50 mL) was cooled in an ice bath and treated with sodium triacetoxyborohydride (10.1 g, 48 mmol). The resulting mixture was then stirred at room temperature overnight. The mixture was treated with 1.0 N aqueous sodium hydroxide (25 mL) and stirred at room temperature for 1 hour. The organic phase was removed and washed with water and saturated aqueous sodium chloride. The solvent was removed under vacuum to give a residue. The residue was purified by chromatography on silica gel, eluting with 60% ethyl acetate/hexane, to give an oil (6.3 g). 1H NMR (300 MHz, CDCl3) δ7.31-7.24 (m, 2H), 6.97-6.94 (m, 2H), 4.82 (bm, 1H), 3.62 (m, 1H), 3.37 (bs, 2H), 2.42 (m, 1H), 2.20 (m, 3H), 1.69-1.21 (m, 12H), 1.45 (s, 9H). Mass spec (ES+) m+/z 377.2 (M+H+).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customThe organic phase was removed
  3. washwashed with water and saturated aqueous sodium chloride
  4. customThe solvent was removed under vacuum
  5. customto give a residue
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with 60% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a26e004a5143423d9d7f840241772914
Source dataset
uspto-grants-2009_01
Patent number
US07479496B2

Reaction notes

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