Lithium tri-s-butylborohydride → Dibenzyl(1S,2S,4S,5R,6R)-2-tert-butoxycarbonylamino-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

HRID 929903Notes

Reaction equation

HRID 929903 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[C:15]1([CH2:21][O:22][C:23]([C@:25]2([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:30][C:29](=[O:31])[C@@H:28]3[C@H:26]2[C@H:27]3[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH2:21]([O:22][C:23]([C@:25]1([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:30][C@H:29]([OH:31])[C@@H:28]2[C@H:26]1[C@H:27]2[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])=[O:24])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 86716590HCID 86716590, compound

Product 1

HCID 71131320Dibenzyl(1S,2S,4S,5R,6R)-2-tert-butoxycarbonylamino-4-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add 1M L-selectride solution in THF (30 mL, 30 mmol) dropwise to a stirred solution of bis[(phenyl)methyl](1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylate (9.15 g, 19.08 mmol) in tetrahydrofuran (20 mL) at −78° C. Stir the resulting orange mixture under nitrogen for 1 hour 45 minutes. Quench with a saturated solution of sodium hydrogen carbonate at −78° C. Dilute with water and ethyl acetate. Separate the layers and wash the organic phase with brine and water. Dry over sodium sulfate, filter and concentrate to dryness to give the crude material as pale yellow oil. Purify the combined material by flash chromatography eluting with ethyl acetate:hexanes (20:80 to 50:50) to give the title product as a single isomer (9.19 g, 100%). MS (m/z): 504 (M+23)

Workup

  1. customQuench with a saturated solution of sodium hydrogen carbonate at −78° C
  2. additionDilute with water and ethyl acetate
  3. customSeparate the layers
  4. washwash the organic phase with brine and water
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to dryness
  8. customto give the crude material as pale yellow oil
  9. customPurify the combined material by flash chromatography
  10. washeluting with ethyl acetate:hexanes (20:80 to 50:50)

Sources & evidence

ORD record
ord-58fa419017ad491f8390cd2b7205e48b
Source dataset
uspto-grants-2016_03
Patent number
US09296710B2

Reaction notes

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