Water → HCID 22856091, compound

HRID 1721195Notes

Reaction equation

HRID 1721195 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[CH2:15]([N:22]1[CH2:30][C@H:29]2[C@H:24]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:26][CH2:27][C:28]2=[O:31])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH4-].O>O1CCCC1.C(OCC)(=O)C>[CH2:15]([N:22]1[CH2:30][C@H:29]2[C@H:24]([C:25]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:26][CH2:27][C@H:28]2[OH:31])[CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 28123BorohydrideHCID 3611392Lithium tri-s-butylborohydrideHCID 10981812HCID 10981812, compound

Product 1

HCID 22856091HCID 22856091, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

4.0 cm3 of a 1M solution of lithium tri-sec-butyl borohydride in tetrahydrofuran is added over 5 minutes to a solution, cooled to 0° C., of 1.3 g of (3aR, 7aR)-2-benzyl-7,7-diphenyl-4-perhydroisoindolone in 6.0 cm3 of tetrahydrofuran. After stirring for 3 hours at 0° C., the reaction mixture is again supplemented with 0.5 cm3 of the 1M solution of borohydride. After 1 hour at 0° C. and the addition of 50 cm3 of water and 50 cm3 of ethyl acetate, the organic phase is decanted, washed with 20 cm3 of water, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The oil obtained is crystallized from 30 cm3 of diisopropyl oxide, the crystals are drained and dried under reduced pressure (2.7 kPa). 0.70 g of (3aR, 4R, 7aR)-2-benzyl-7,7-diphenyl-4-perhydroisoindolol is obtained in the form of white crystals; melting point 154° C.

Workup

  1. waitAfter 1 hour at 0° C.
  2. customthe organic phase is decanted
  3. washwashed with 20 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe oil obtained
  7. customis crystallized from 30 cm3 of diisopropyl oxide
  8. customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-03ef7a0aee2f44d89fb1aa0303cb7132
Source dataset
uspto-grants-1996_04
Patent number
US05508433

Reaction notes

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