Naphthalene → 1-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol

HRID 1254321ノート

反応式

HRID 1254321 の反応式
[OH:1][C:2]1([CH2:8][CH:9]([NH:19][CH3:20])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1C2C(=CC=CC=2)C=CC=1.C([O-])([O-])=O.[K+].[K+].[C:37]([O:46]N1C(=O)CCC1=O)([O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])=O>C1COCC1.O>[C:14]([O:13][C:12]([NH:11][CH2:10][CH:9]([N:19]([CH3:20])[C:37]([O:39][CH2:40][CH2:41][Si:42]([CH3:43])([CH3:44])[CH3:45])=[O:46])[CH2:8][C:2]1([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:18])([CH3:16])([CH3:17])[CH3:15]

参加物

6

反応物 4

HCID 931NaphthaleneHCID 11430Potassium CarbonateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 59382899Tert-butyl 3-(1-hydroxycyclohexyl)-2-(methylamino)-propylcarbamate

生成物 1

HCID 671883231-(3-(t-butoxy-carbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol収率 86%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a solution of above mixture of tert-butyl 3-(1-hydroxycyclohexyl)-2-(methylamino)-propylcarbamate and naphthalene in 3:1 THF/H2O v/v (4 mL) was added K2CO3 (100 mg, 0.72 mmol), followed by Teoc-OSu (70 mg, 0.27 mmol). The resulting solution was stirred at rt for 30 min and the organic solvent was removed under reduced pressure. The residue was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried, filtered, and concentrated under vacuum. The residue was chromatographed on silica gel to give 1-(3-(t-butoxycarbonylamino)-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propyl)cyclohexanol (100 mg, 86% for three steps). MS m/z 453 (M+Na+).

後処理

  1. customthe organic solvent was removed under reduced pressure
  2. extractionThe residue was extracted with EtOAc (2×)
  3. washThe combined organic phases were washed with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-26ea10b2cf354b2b83fdce4e195269f4
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

反応ノート

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