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

HRID 276262

反応式

HRID 276262 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b8be7ca67a4642e3b1d85e29e53d31d9
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

関連ノート

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