Hydrochloric Acid → 2-benzyl 3-methyl (2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate

HRID 61440ノート

反応式

HRID 61440 の反応式
[CH2:1]([N:8]1[CH2:13][C@H:12]([O:14]C(OCC)C)[CH2:11][C@H:10]([C:20]([O:22][CH3:23])=[O:21])[C@H:9]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.Cl.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH2:1]([N:8]1[CH2:13][C@H:12]([OH:14])[CH2:11][C@H:10]([C:20]([O:22][CH3:23])=[O:21])[C@H:9]1[C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 1317319252-benzyl 3-methyl (2S,3S,5R)-1-benzyl-5-(1-ethoxyethoxy)piperidine-2,3-dicarboxylate

生成物 1

HCID 1317319262-benzyl 3-methyl (2S,3S,5R)-1-benzyl-5-hydroxypiperidine-2,3-dicarboxylate収率 100.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-benzyl 3-methyl(2S,3S,5R)-1-benzyl-5-(1-ethoxyethoxy)piperidine-2,3-dicarboxylate (5.70 g, 0.0125 mol) in 100 mL of THF was added 20 mL of water followed by 20 mL of 1N HCl. The mixture was stirred at rt fro 1 h. After diluted with EtOAc, the mixture was neutralized with 1N NaOH, washed with brine, dried. The residue obtained after concentration was applied on silical, eluting with 0 to 50% EtOAc in hexane, to provide the alcohol compound (4.80 g, 89.6%). MS (ESI): (M+H)+=384.2.

後処理

  1. washwashed with brine
  2. customdried
  3. customThe residue obtained
  4. concentrationafter concentration
  5. washeluting with 0 to 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-ad02acc0e474490f98a85f314c1e9dbf
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

反応ノート

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