Tetrahydrofuran → HCID 68765590, compound

HRID 1171547Notes

Reaction equation

HRID 1171547 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C@@H:12]1[CH:25]=[CH2:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B1C2CCCC1CCC2.C1C[O:40]CC1>>[CH2:1]([O:8][C:9](=[O:27])[NH:10][C@H:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:13][C@@H:12]1[CH2:25][CH2:26][OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 789669-Borabicyclo(3.3.1)nonaneHCID 68767788HCID 68767788, compound

Product 1

HCID 68765590HCID 68765590, compound

Procedure

The compound [(1S,2R,4R)-[4-tert-butoxycarbonylamino-2-(vinyl)-cyclohexyl]-carbamic acid benzyl ester (0.82 g, 2.2 mmol) was dissolved in THF (15 mL). The resultant solution was cooled to 0° C. and charged with 9-BBN (11 mL of a 0.5 M solution in THF). The mixture was stirred for 20 h at RT and then quenched sequentially with aqueous sodium acetate (0.6 g in 1.5 mL water) and 30% hydrogen peroxide (1.5 mL). This was stirred at RT for 14 h and partitioned between EtOAc and sat. NaHCO3. The aqueous phase was extracted with EtOAc, and the combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to afford [(1S,2R,4R)-[4-tert-butoxycarbonylamino-2-(hydroxyethyl)-cyclohexyl]-carbamic acid benzyl ester (0.42 g) as a white foam. MS found: (M+H)+=393.

Workup

  1. customquenched sequentially with aqueous sodium acetate (0.6 g in 1.5 mL water) and 30% hydrogen peroxide (1.5 mL)
  2. stirringThis was stirred at RT for 14 h
  3. custompartitioned between EtOAc and sat. NaHCO3
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-be9c0fc133ad4ddb99da8bb215c00335
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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