Hydrochloric Acid → HCID 58380973, compound

HRID 45190Notes

Reaction equation

HRID 45190 reaction equation
[O:1]=[C:2]1[CH2:7][C@@H:6]2[CH2:8][C@H:3]1[CH2:4][C@:5]2([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]#[N:10].[BH4-].[Na+].[Na+].[Cl-].Cl>C(O)C>[OH:1][CH:2]1[CH2:7][C@@H:6]2[CH2:8][C@H:3]1[CH2:4][C@:5]2([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]#[N:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 58380931HCID 58380931, compound

Product 1

HCID 58380973HCID 58380973, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.9 g (4.3 mmol) of (1S,2S,4S)-5-Oxo-2-phenyl-bicyclo[2.2.1]heptane-2-carbonitrile (86) were dissolved using 20 mL of ethanol and 161 mg (4.3 mmol) of NaBH4 was added at −70° C. The mixture was stirred at ambient temperature for 1 h, 100 mL of a saturated aqueous NaCl-solution was added and the pH adjusted to 2-3 using aqueous HCl-solution. The mixture was extracted three times using 50 mL of ethyl acetate each. The organic layer was dried over MgSO4 and evaporated to yield 0.9 g of (87) as a single diastereomer as a colourless oil. Rt=0.76 min (Method 18). Detected mass: 214.1 (M+H+)

Workup

  1. additionwas added at −70° C
  2. extractionThe mixture was extracted three times
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-f03609ebd12a44a29d4bb056112a3fa6
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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