Methanol → (R)-2-Methyl-N-((R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfinamide

HRID 1844410ノート

反応式

HRID 1844410 の反応式
[BH4-].[Na+].[CH3:3][C:4]([S@:7]([N:9]=[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=2)[CH2:12][CH2:11]1)=[O:8])([CH3:6])[CH3:5].C1COCC1.CO>C(=O)=O>[CH3:6][C:4]([S@:7]([NH:9][C@H:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=2)[CH2:12][CH2:11]1)=[O:8])([CH3:3])[CH3:5]

参加物

6

反応物 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86729181(R)-2-methyl-N-(6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ylidene)propane-2-sulfinamide

生成物 1

HCID 89478184(R)-2-Methyl-N-((R)-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfinamide収率 26.7%

試薬・触媒・溶媒 1

HCID 280Carbon Dioxide溶媒

反応条件

温度
0 °C

実験手順

Sodium borohydride (756 mg, 20.0 mmol) was stirred in a round-bottomed flask under argon at −40 to −50° C. The reaction mixture of Intermediate 15A was added dropwise to the flask, and THF was added to the reaction mixture (ca. 0.6 M). The resulting mixture was allowed to warm up to 0° C. during 1.5 h period. The reaction mixture was cooled in dry ice and MeOH was added dropwise until gas evolution stopped. The mixture was stirred at rt for 20 min, filtered through Celite® and rinsed with EtOAc then CH2Cl2. The filtrate was washed with brine (2×) and dried over MgSO4, filtered and concentrated. The residue was purified on ISCO (hexanes/EtOAc) to give Intermediate 15B (370 mg, 1.21 mmol, 26.7% yield) as colorless crystals. LC-MS (ESI) 306.0 (M+H), RT=2.10 min (Method B).

後処理

  1. filtrationfiltered through Celite®
  2. washrinsed with EtOAc
  3. washThe filtrate was washed with brine (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on ISCO (hexanes/EtOAc)

出典と根拠

ORDレコード
ord-a50be4ff2ca64f23af290c20a39cf7d8
出典データセット
uspto-grants-2015_02
特許番号
US08946430B2

反応ノート

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