Tryptophol → 6-Benzyloxy-1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

HRID 1111610ノート

反応式

HRID 1111610 の反応式
[CH:1]1C=CC2NC=C(CCO)C=2C=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:19]([O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[C:30]2[C:36](=O)[C:37]([O:39][CH2:40][CH3:41])=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31]1[C:40]([CH3:41])([CH3:1])[O:39][CH2:37][CH2:36][C:30]2=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 10685TryptopholHCID 253116Ethyl [5-(benzyloxy)-1H-indol-3-yl](oxo)acetateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 199357106-Benzyloxy-1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

5-Benzyloxy-3-tryptophol (II; R2, R3, R4 and R5 = H, R6 = 5-benzyloxy and X1 = OH), m.p. 93°-95° C., is prepared by lithium aluminum hydride reduction of ethyl 5-benzyloxy-3-indoleglyoxalate (British Pat. No. 778,823) according to the procedure of Example 309. Subsequent treatment of 5-benzyloxy-3-tryptophol with the ketone, acetone, according to the procedure of Example 785 affords 6-benzyloxy-1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole (VII; R1M CH3), nmr (CDCl3) δ1.53 (6H), 2.73 (t, 2H), 4.03 (t, 2H), 5.10 (2H), 6.67-7.83 (9H). The latter compound is then N-alkylated with the organic halide, dimethylaminoethyl chloride, according to the procedure of Example 838 to afford 6-benzyloxy-1,1-dimethyl-9-[2-(dimethylamino)ethyl]-1,3,4,9-tetrahydropyrano[3,4-b]indole, which on treatment with hydrochloric acid gives the corresponding hydrochloric acid addition salt thereof, m.p. 209° C.

出典と根拠

ORDレコード
ord-a1e7bbd393c0431eaea589c197432f3f
出典データセット
uspto-grants-1978_10
特許番号
US04118394

反応ノート

読み込み中…