2-[2-(Hydroxymethyl)pyrrolidin-1-yl]acetonitrile → [1-(2-Amino-ethyl)-pyrrolidin-2-yl]-methanol

HRID 226250

反応式

HRID 226250 の反応式
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:8][C:9]#[N:10].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:10][CH2:9][CH2:8][N:4]1[CH2:5][CH2:6][CH2:7][CH:3]1[CH2:2][OH:1]

参加物

4

反応物 2

HCID 115137632-[2-(Hydroxymethyl)pyrrolidin-1-yl]acetonitrileHCID 21226445Aluminium lithium hydride

生成物 1

HCID 21283823[1-(2-Amino-ethyl)-pyrrolidin-2-yl]-methanol収率 63%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The method follows that of S6 using 2-hydroxymethyl-pyrrolidin-1-yl-acetonitrile (19.5 g, 0.139 mol), LiAlH4 (15.84 g, 0.417 mol) and dry THF (150 mL). The title-compound (12.5 g, 63%) was afforded as straw-coloured oil by kugelrohr distillation (142° C., 0.3 mbar). δH (250 MHz; CDCl3); 1.6-1.9 (m, 4H, CH2CH2CH2, CH2CH2CH), 1.98 (s (broad), 3H, NH2, OH), 2.3 (m, 1H), 2.45 (m, 1H), 2.55 (m, 1H), 2.75-2.85 (m, 3H), 3.19 (m, 1H, NCHCH2), 3.4 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH), 3.6 (2×d, 1H, J=3 Hz and J=11 Hz, 1×CHCH2OH); IR υmax/cm−1; 3375 (NH2), 3300 (NH2), 3200 (OH), 2970-2800 (CH2, CH3), 1600, 1475, 1375, 1230 and 1060; FAB MS, m/z(M+H)+ 145.

出典と根拠

ORDレコード
ord-951eb1dc297f4538bc06d40d52b4c8c5
出典データセット
uspto-grants-2009_07
特許番号
US07557215B2

関連ノート

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