HCID 68476611, compound → HCID 68477452, compound

HRID 75162Notes

Reaction equation

HRID 75162 reaction equation
[OH:1][C@@H:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:3]([NH:5][C:6]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=O)[CH3:4]>C1COCC1.Cl>[C:8]12([CH2:6][NH:5][C@H:3]([CH3:4])[C@H:2]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[OH:1])[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][CH:10]([CH2:16]3)[CH2:9]1)[CH2:17]2

Participants

4

Reactant 1

HCID 68476611HCID 68476611, compound

Product 1

HCID 68477452HCID 68477452, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)adamantane-1-carboxamide (3.07 g, 9.8 mmol) in dry THF (50 mL) was cooled in an ice bath and 1M BH3 in THF (50 mL, 50 mmol) was added. The ice bath was allowed to melt and the mixture was stirred over the weekend at rt. The mixture was poured into 5% aq HCl (50 mL). The mixture was concentrated on the rotary evaporator to leave a white solid which was taken up in 5% aq HCl (75 mL) and washed with ether (150 mL). The aqueous layer was made strongly basic by addition of NaOH and extracted with EtOAc (2×100 mL). The combined EtOAc extracts were dried over MgSO4 and concentrated to afford (1S,2R)-2-(1-adamantylmethylamino)-1-phenylpropan-1-ol (2.28 g, 77%) as an oil. LC-MS (3 min) tR=1.32 min, m/z=300.

Workup

  1. concentrationThe mixture was concentrated on the rotary evaporator
  2. customto leave a white solid which
  3. washwashed with ether (150 mL)
  4. additionThe aqueous layer was made strongly basic by addition of NaOH
  5. extractionextracted with EtOAc (2×100 mL)
  6. dry with materialThe combined EtOAc extracts were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ab2a4e5d5da84c91aa65effef22d93d5
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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