Ethyl Acetate → HCID 178487963, compound

HRID 633820Notes

Reaction equation

HRID 633820 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:34])[NH:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH2:16][C:17]2[C:18](=[O:33])[O:19][C:20]3[CH:21]=[N:22][C:23]4[C:28]([C:29]=3[CH:30]=2)=[CH:27][C:26]([O:31][CH3:32])=[CH:25][CH:24]=4)[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].C(OCC)(=O)C>CO>[C:3]([O:7][C:8](=[O:34])[NH:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([CH2:16][CH:17]([CH2:30][C:29]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([O:31][CH3:32])[CH:27]=3)[N:22]=[CH:21][C:20]=2[OH:19])[CH2:18][OH:33])[CH2:14][CH2:15]1)([CH3:4])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 178487832HCID 178487832, compound

Product 1

HCID 178487963HCID 178487963, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (86 mg, 2.28 mmol, 10.0 eq) is added at 0° C. to a stirred suspension of [trans-4-(6-methoxy-2-oxo-2H-1-oxa-9-aza-phenanthren-3-ylmethyl)-cyclohexyl]-carbamic acid tert-butyl ester (100 mg, 0.23 mmol, 1.0 eq) in methanol (10 mL). After 8 hours stirring at room temperature, the reaction mixture is quenched with ammonium chloride aqueous solution (10 mL), methanol is removed and the resulting residue is extracted with ethyl acetate (3×20 mL) and brine (20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 2:1, v/v) to afford {trans-4-[3-hydroxy-2-(3-hydroxy-6-methoxy-quinolin-4-ylmethyl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (60 mg, 59% yield).

Workup

  1. customthe reaction mixture is quenched with ammonium chloride aqueous solution (10 mL), methanol
  2. customis removed
  3. extractionthe resulting residue is extracted with ethyl acetate (3×20 mL) and brine (20 mL)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product that
  8. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-fdef15fe1a0347a2bd1b6a03812456de
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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