Sodium borohydride → [1-(Cyclopentylamino)cyclopentyl]methanol

HRID 276262

Reaction equation

HRID 276262 reaction equation
[CH2:1]1[C:5]2([CH2:13][O:12][C:7]3([CH2:11][CH2:10][CH2:9][CH2:8]3)[NH:6]2)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CCO.O>[CH:7]1([NH:6][C:5]2([CH2:13][OH:12])[CH2:1][CH2:2][CH2:3][CH2:4]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1831628713-aza-6-oxadispiro[4.2.4.I]tridecane

Product 1

HCID 18316183[1-(Cyclopentylamino)cyclopentyl]methanolYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 6-aza-12-oxadispiro[4.1.4.2]tridecane (124 g, 0.69 mol) dissolved in EtOH (600 mL) held at −13° C. with an ice/MeOH bath was added NaBH4 (38 g, 1.0 mol, 1.45 equiv.) in portions at a rate that the temp. did not exceed 10° C. (approximately 30 min.). The reaction mixture was allowed to warm to room temp. and stirred overnight. The reaction mixture was diluted with water (500 mL) and concentrated under reduced pressure. The residual paste was separated between EtOAc (1 L) and water (600 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield 1-(cyclopentylamino)-1-(hydroxymethyl)cyclopentane as a white powder (107 g, 85%): 1H NMR (CDCl3) δ1.23-1.28 (m, 2H), 1.46-1.57 (m, 8H), 1.58-1.69 (m, 4H), 1.82-1.86 (m, 2H), 2.94-3.06 (m, 1H,), 3.30 (s, 2H).

Workup

  1. customheld at −13° C. with an ice/MeOH bath
  2. customdid not exceed 10° C.
  3. custom(approximately 30 min.)
  4. temperatureto warm to room temp.
  5. concentrationconcentrated under reduced pressure
  6. customThe residual paste was separated between EtOAc (1 L) and water (600 mL)
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8be7ca67a4642e3b1d85e29e53d31d9
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Linked notes

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