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Sodium borohydride → (R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester

HRID 77330
Notes
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Reaction equation

HRID 77330 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22](=[O:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])[CH3:2].[BH4-].[Na+]>O1CCCC1CCO>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]([OH:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:8])=[O:9])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86653278(R)-N-naphthalene-2-sulfonyl (3-oxo-cyclohepty)glycine ethyl ester

Product 1

HCID 86653277(R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)—N-naphthalene-2-sulfonyl (3-oxo-cyclohepty)glycine ethyl ester (1.05 g, 2.61 mmol) in tetrahydrofuran-ethanol (20 mL, 1:1) at 0° C. is added sodium borohydride (0.147 g, 3.88 mmol) and the reaction is stirred at 0° C. for 1 hour. The reaction was quenched at 0° C. with citric acid (10% aqueous), and the solvents were removed in vacuo. The residue was dissolved in water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by column chromatography (50% hexanes-ethyl acetate) to afford the title compound as a white solid (0.90 g, 85% yield). LCMS (m/z): 406.14 (M+1), 404.13 (M−1).

Workup

  1. customThe reaction was quenched at 0° C. with citric acid (10% aqueous)
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (50% hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-48ea1697e4ac4b93ba100314d0fe3485
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841291B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes