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Triphenylphosphine → (3aR,4R,5R,6R,7aS)-4,5-Bis(benzyloxy)-6-((benzyloxy)methyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole

HRID 2274310
ノート
印刷プレビュー

反応式

HRID 2274310 の反応式
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:12][C@@H:11](O)[C@@H:10]1[NH:33][C:34]([N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)=[S:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:1]([O:8][C@@H:9]1[C@H:10]2[N:33]=[C:34]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[S:35][C@H:11]2[CH2:12][C@H:13]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:14]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 86727204N-((1S,2R,3R,4R,6R)-2,3-bis(benzyloxy)-4-((benzyloxy)methyl)-6-hydroxycyclohexyl)pyrrolidine-1-carbothioamide

生成物 1

HCID 67480335(3aR,4R,5R,6R,7aS)-4,5-Bis(benzyloxy)-6-((benzyloxy)methyl)-2-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydrobenzo[d]thiazole収率 84%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of N-((1S,2R,3R,4R,6R)-2,3-bis(benzyloxy)-4-((benzyloxy)methyl)-6-hydroxycyclohexyl)pyrrolidine-1-carbothioamide (0.260 g, 0.464 mmol) and triphenylphosphine (0.183 g, 0.700 mmol) in anhydrous THF (6.0 mL) was added DIAD (0.131 g, 0.650 mmol). After addition the mixture was stirred at room temperature for 60 h. The solvent was evaporated under reduced pressure, and the residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:10 to 1:4), affording as a colorless oil (0.21 g, 84%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.42 (m, 2H), 7.34-7.23 (m, 13H), 4.95 (d, J=11.6 Hz, 1H), 4.86 (d, J=11.0 Hz, 1H), 4.76 (d, J=11.6 Hz, 1H), 4.56 (d, J=11.0 Hz, 1H), 4.50-4.43 (m, 2H), 3.80 (d, J=7.6 Hz, 1H), 3.78-3.76 (m, 2H), 3.68 (dd, J=4.0, 9.0 Hz, 1H), 3.57-3.43 (m, 4H), 3.13 (d, J=6.2 Hz, 1H), 2.89-2.88 (m, 1H), 2.28-2.23 (m, 1H), 2.05-2.02 (m, 1H), 2.00-1.90 (m, 4H), 1.87-1.82 (m, 1H).

後処理

  1. additionAfter addition the mixture
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 1:10 to 1:4)

出典と根拠

ORDレコード
ord-3fd5a4b4f3cf4287b813904f385384d0
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09126957B2

反応ノート

読み込み中…

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