Sodium borohydride → HCID 86586740, compound

HRID 2088195Notes

Reaction equation

HRID 2088195 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@H:10]([O:23][C@H:24]([C:39](OC)=[O:40])[C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1)[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1[C@@H]2[C@H](C(OC(C)(C)C)=O)C[C@@]1(C1C=CC=CC=1)[C@H](O[C@@H](C(OC)=O)C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1)CC2)C1C=CC=CC=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@H:10]([O:23][C@H:24]([C:25]1[CH:26]=[C:27]([C:35]([F:36])([F:37])[F:38])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1)[CH2:39][OH:40])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 86586741HCID 86586741, compoundHCID 86586742HCID 86586742, compound

Product 1

HCID 86586740HCID 86586740, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1R*,2R*,5S*,6R*)-8-Benzyl-2-{(1S*)-1-[3,5-bis(trifluoromethyl)phenyl]-(methoxycarbonyl)methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane and (1R*,2R*,5S*,6R*)-8-benzyl-2-{(1R*)-1-[3,5-bis(trifluoromethyl)phenyl]-(methoxycarbonyl)methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 125; 0.99 g, 1.5 mmol) in methanol (15 ml) at 0° C. was treated with sodium borohydride (55 mg, 1.4 mmol) and stirred at room temperature. The reaction was quenched with acetone and concentrated in vacuo. The residue was partitioned between ethyl acetate and water, the organics were separated, dried (MgSO4), filtered and concentrated in vacuo to afford the title compounds as a clear foam (869 mg, 92%).

Workup

  1. customThe reaction was quenched with acetone
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe organics were separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ceae2a9be8f49bb9eb6e6af9e206b87
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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