Sodium Hydroxide → ((1R,3R)-1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentyl)methanol

HRID 1511852Notes

Reaction equation

HRID 1511852 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C@:8]1([C:30](OC)=[O:31])[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:15][CH:14]=2)[CH2:9]1.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC.C1COCC1.O>[NH2:7][C@:8]1([CH2:30][OH:31])[CH2:12][CH2:11][C@@H:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][CH2:21][O:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:15][CH:14]=2)[CH2:9]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57554604(1R,3R)-methyl 1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentanecarboxylate

Product 1

HCID 57554621((1R,3R)-1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentyl)methanolYield 81.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of LAH (7.83 g, 206 mmol) in Et2O (500 mL) at about 0° C. was added a solution of (1R,3R)-methyl 1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentanecarboxylate (25 g, 68.8 mmol) in THF (100 mL). After about 2 hours water (7.8 mL) followed by 2N NaOH (7.8 mL) followed by water (15 mL) was added. After stirring for about 15 hours Na2SO4 and Celite® was added to the reaction mixture and the slurry was filtered, rinsing with EtOAc. The filtrate was concentrated in vacuo to provide ((1R,3R)-1-amino-3-(4-(3-(benzyloxy)prop-1-ynyl)phenyl)cyclopentyl)methanol (25 g, 55.9 mmol, 81% yield) as an brown oil.

Workup

  1. additionwas added
  2. additionwas added to the reaction mixture
  3. filtrationthe slurry was filtered
  4. washrinsing with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9dd0a2339ffa462d8a88678bc9f8a79b
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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