Triethylamine → tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

HRID 712035ノート

反応式

HRID 712035 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](O)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.CO>[OH:16][CH2:15][CH:11]1[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 44203163-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

生成物 1

HCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate収率 92%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a mixture of 3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (from Alfa Aesar, 3.3 g, 14 mmol) and triethylamine (3.8 mL, 27 mmol) in tetrahydrofuran (40 mL) at 0° C. was added dropwise ethyl chloroformate (1.9 mL, 20 mmol). The mixture was stirred at 0° C. for 10 min and then at room temperature for 20 min. The mixture was filtered to remove the white solid and then cooled to 0° C. A mixture of sodium tetrahydroborate (1.0 g, 27 mmol) and methanol (1 mL) was added slowly. The mixture was stirred at room temperature for 1 h. The mixture was quenched with 1N aq. HCl solution and extracted with EtOAc. The extracts were concentrated and purified on silica gel column (eluting with 75% EtOAc in hexanes) to give the desired product (2.88 g, 92%). LCMS calculated for C13H23NO3Na (M+Na)+: m/z=252.2. Found: 252.1.

後処理

  1. waitat room temperature for 20 min
  2. filtrationThe mixture was filtered
  3. customto remove the white solid
  4. temperaturecooled to 0° C
  5. additionwas added slowly
  6. stirringThe mixture was stirred at room temperature for 1 h
  7. customThe mixture was quenched with 1N aq. HCl solution
  8. extractionextracted with EtOAc
  9. concentrationThe extracts were concentrated
  10. custompurified on silica gel column (eluting with 75% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-7ebf58bd530c4075a2707355eef48acc
出典データセット
uspto-grants-2015_11
特許番号
US09181271B2

反応ノート

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