Pyridine → Benzyl ((1S,3R)-3-carbamoylcyclohexyl)carbamate

HRID 526946

反応式

HRID 526946 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([C:18]([OH:20])=O)[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:21]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[C:18]([C@@H:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:13]1)(=[O:20])[NH2:21]

参加物

6

反応物 4

HCID 1049PyridineHCID 14013Ammonium Bicarbonate2 回HCID 90495Di-tert-butyl dicarbonate2 回HCID 23584443rel-(1R,3S)-3-(((Phenylmethoxy)carbonyl)amino)cyclohexanecarboxylic acid2 回

生成物 1

HCID 68007396Benzyl ((1S,3R)-3-carbamoylcyclohexyl)carbamate収率 91%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of (1R,3S)-3-Benzyloxycarbonylaminocyclohexanecarboxylic acid, 18c, (10.0 g, 36.1 mmol) in 1,4-dioxane (300 mL) was added pyridine (2.9 mL, 36.1 mmol), followed by di-tert-butyl dicarbonate (10.7 mL, 46.9 mmol) and ammonium bicarbonate (10.1 g, 126.2 mmol). After 3 hours, another portion of di-tert-butyl dicarbonate (1.5 g, 6.8 mmol) and ammonium bicarbonate (1.5 g, 6.8 mmol) was added and stirring was continued overnight. The reaction was quenched by addition of 2N HCl (400 mL) and stirred for 1 hour. The resulting suspension was filtered under reduced pressure, washed with 2N HCl (50 mL), water (8×50 mL) and hexanes (3×50 mL) and vacuum dried to provide benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (9.1 g, 91%) as a white solid.

後処理

  1. waitwas continued overnight
  2. customThe reaction was quenched by addition of 2N HCl (400 mL)
  3. stirringstirred for 1 hour
  4. filtrationThe resulting suspension was filtered under reduced pressure
  5. washwashed with 2N HCl (50 mL), water (8×50 mL) and hexanes (3×50 mL) and vacuum
  6. customdried

出典と根拠

ORDレコード
ord-0e5251041f9344d4adf8fb87c9bc839f
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

関連ノート

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