Hydrochloric Acid → 1,4'-Bipiperidin-4-ol

HRID 1060820

反応式

HRID 1060820 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=O)(C)(C)C.OC1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClC(Cl)C.CO.C(O)(=O)C>[N:8]1([CH:6]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:9][CH2:10][CH:11]([OH:14])[CH2:12][CH2:13]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 79341Piperidin-4-olHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 220613421,4'-Bipiperidin-4-ol

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

4-Oxo-piperidine-1-carboxylic acid tert-butyl ester (20 g) and 4-hydroxypiperidine (6.7 g) were stirred together in dichloroethane (200 ml) with acetic acid (4 ml) at RT for 30 minutes. Sodium triacetoxyborohydride (23 g) was then added and the mixture stirred at RT overnight. The mixture was evaporated to dryness and the residue taken into water, extracted with diethyl ether (3×200 ml), the aqueous was basified to pH 9-10 and extracted with dichloromethane (3×200 ml). The dichloromethane extracts were combined, dried (MgSO4) and evaporated to leave an oil (19 g; same compound as Example 9 step 1). The oil was dissolved in methanol (300 ml) and treated with concentrated hydrochloric acid (5 ml). The mixture was stirred overnight and then evaporated to dryness to leave the title compound as the hydrochloride salt (15 g).

後処理

  1. customThe mixture was evaporated to dryness
  2. extractionextracted with diethyl ether (3×200 ml)
  3. extractionextracted with dichloromethane (3×200 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto leave an oil (19 g; same compound as Example 9 step 1)
  7. stirringThe mixture was stirred overnight
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-ce78c81427db4a43bfe750158d2f3136
出典データセット
uspto-grants-2003_02
特許番号
US06525070B2

関連ノート

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