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

HRID 276262

반응식

HRID 276262 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b8be7ca67a4642e3b1d85e29e53d31d9
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

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