Hydrochloric Acid → HCID 67074964, compound

HRID 38453Notes

Reaction equation

HRID 38453 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([C:14]3=[O:21])[CH2:12]1)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]12[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH:14]3[OH:21])[CH2:20]1)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 58192798(4-Oxo-adamantan-1-yl)-carbamic acid benzyl ester

Product 1

HCID 67074964HCID 67074964, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

865 mg of (4-Oxo-adamantan-1-yl)-carbamic acid benzyl ester (12) were dissolved in 15 mL of THF and 109 mg of sodium borohydride were added at 0° C. Stirring was continued for 2 h, then the reaction mixture was acidified by addition of 2M HCl. The reaction mixture was extracted three times with ethyl acetate and the combined organic layer was dried over sodium sulphate and evaporated. The resulting oil was subjected to HPLC separation to give 463 mg of the desired product as a cis/trans mixture along with 119 mg of the cis derivative (13a) and 10 mg of the trans derivative (13b). 13a: Rt=1.37 min (Method 3). Detected mass: 302.3 (M+H+). 13b: Rt=1.39 min (Method 3). Detected mass: 302.3 (M+H+);

Workup

  1. extractionThe reaction mixture was extracted three times with ethyl acetate
  2. dry with materialthe combined organic layer was dried over sodium sulphate
  3. customevaporated
  4. customThe resulting oil was subjected to HPLC separation

Sources & evidence

ORD record
ord-ec77ce9c573249a5ad062b1c826d015c
Source dataset
uspto-grants-2013_09
Patent number
US08524737B2

Reaction notes

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