Water → HCID 22856091, compound

HRID 2400012Notes

Reaction equation

HRID 2400012 reaction equation
[Li].[CH2:2]([N:9]1[CH2:17][C@H:16]2[C@H:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:13][CH2:14][C:15]2=[O:18])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].O>O1CCCC1.C(OCC)(=O)C>[CH2:2]([N:9]1[CH2:17][C@H:16]2[C@H:11]([C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:13][CH2:14][C@H:15]2[OH:18])[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 28123BorohydrideHCID 3028194LithiumHCID 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-butylboro-hyride 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., 0.5 cm3 of the 1M solution of borohydride is again added to the reaction mixture. After 1 hour at 0° C., followed by 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-6242e06df56c46428dd8b31c7a8b3dba
Source dataset
uspto-grants-1995_09
Patent number
US05451601

Reaction notes

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