Hydrochloric Acid → HCID 86730046, compound

HRID 516950Notes

Reaction equation

HRID 516950 reaction equation
[NH2:1][C:2]1([C:23](OC)=[O:24])[CH2:6][CH2:5][CH:4]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][C@H:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][CH2:10][C:9]=3[CH:8]=2)[CH2:3]1.[BH4-].[Na+].Cl.[OH-].[Na+]>CCO.C(Cl)Cl>[NH2:1][C:2]1([CH2:23][OH:24])[CH2:6][CH2:5][CH:4]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][C@H:12]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][CH2:10][C:9]=3[CH:8]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86730047HCID 86730047, compound

Product 1

HCID 86730046HCID 86730046, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 1-amino-3-((R)-6-hexyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopentanecarboxylate (I-8F, 5.7 g, 16 mmol) was dissolved in EtOH (60 mL) and methylene chloride (15 mL). Sodium borohydride (2.5 g, 67 mmol) was added. The mixture was stirred at room temperature overnight. Hydrochloric acid (6 N aqueous, 40 mL) was added slowly at 0° C. to make pH approximately 1. After the mixture was stirred at room temperature for 60 min, sodium hydroxide (10 g in 20 mL of water) was added to make pH approximately 12. The mixture was stirred at room temperature for 40 min before being concentrated to remove organic solvents. The aqueous residue was diluted with water (20 mL) and extracted with EtOAc (100 mL, 2×50 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate, decolored by charcoal, filtered through CELITE® pad, and concentrated under reduced pressure to give (1-amino-3-((R)-6-hexyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopentyl)methanol (5.0 g, 15 mmol) as a white solid.

Workup

  1. stirringAfter the mixture was stirred at room temperature for 60 min
  2. stirringThe mixture was stirred at room temperature for 40 min
  3. concentrationbefore being concentrated
  4. customto remove organic solvents
  5. additionThe aqueous residue was diluted with water (20 mL)
  6. extractionextracted with EtOAc (100 mL, 2×50 mL)
  7. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  8. filtrationfiltered through CELITE® pad
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9e35de12e7c4032b7a94a81df17f292
Source dataset
uspto-grants-2015_08
Patent number
US09115054B2

Reaction notes

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