Cyclopentylamine → Tert-butyl 2-(cyclopentylamino)acetate

HRID 127625ノート

反応式

HRID 127625 の反応式
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CCOCC>[C:19]([O:18][C:16](=[O:17])[CH2:15][NH:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:22])([CH3:21])[CH3:20]

参加物

5

反応物 3

HCID 2906CyclopentylamineHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetate

生成物 1

HCID 13298943Tert-butyl 2-(cyclopentylamino)acetate収率 66%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a chilled (0°-5° C.) and stirred ethereal solution (500 ml) containing cyclopentyl amine (75 g, 0.88 mol) and triethyl amine (101 g, 1.0 mol) was added t-butyl bromoacetate (136.5 g, 0.7 mol) in ether (300 ml). The reaction mixture was stirred overnight. The ethereal mixture was then concentrated and the residue redissolved in methylene chloride (750 ml). This solution was washed with saturated aqueous sodium bicarbonate (1000 ml), water (2×3000 ml), and brine (2000 ml). The organic portion was separated, dried over MgSO4, filtered and evaporated yielding N-cyclopentylglycine t-butyl ester (92 g, 66%) as a brown oil which slowly crystallized on standing.

後処理

  1. temperatureTo a chilled (0°-5° C.)
  2. concentrationThe ethereal mixture was then concentrated
  3. dissolutionthe residue redissolved in methylene chloride (750 ml)
  4. washThis solution was washed with saturated aqueous sodium bicarbonate (1000 ml), water (2×3000 ml), and brine (2000 ml)
  5. customThe organic portion was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-19059f66fe404d81bba0e4a7822a2b75
出典データセット
uspto-grants-1981_03
特許番号
US04256761

反応ノート

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