Ammonia → HCID 54394851, compound

HRID 1248019Notes

Reaction equation

HRID 1248019 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.N.C([BH3-])#N.[Na+].[BH4-].[Na+].[Li].[Na]>>[CH2:1]1[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

7

Reactant 6

HCID 222Ammonia2×HCID 70461,2,3,4-Tetrahydroisoquinoline2×HCID 3028194LithiumHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 5360545Sodium

Product 1

HCID 54394851HCID 54394851, compound

Procedure

heating a mixture of an amine compound of the formula 4 ##STR4## and pure acid compound, formula 5 R1 ? ? ##STR5## at 200° C. for about 2 hours under argon or other inert gas to obtain amide compound 6 of the following formula ##STR6## (b) contacting compound 6 with phosphorous oxychloride to produce the 1,2-dehydro derivative of compound 7 shown below: ##STR7## which need not be isolated; (c) neutralizing the 1,2-dehydro derivative of compound 7 with aqueous ammonia and reducing with sodium cyanoborohydride or sodium borohydride to give racemic 7 which is then resolved by optically active acids to the compound tetrahydroisoquinoline (+)-7 to (-)-7 ##STR8## (d) treating of (-)-7 with lithium or sodium in liquid ammonia as a reducing agent to give hexahydroisoquinoline, compound (-)-8 ##STR9## and formylating compound (-)-8 to give 10 ##STR10## and introducing a protective group for the nitrogen in the subsequent steps of the reaction where the reagent for formylation of 8 to 10 is phenylformate chloral or ethyl formate

Workup

  1. customneed not be isolated
  2. customto give racemic 7 which

Sources & evidence

ORD record
ord-e59cadc108a94469a058ee7c87706ebd
Source dataset
uspto-grants-1985_06
Patent number
US04521601

Reaction notes

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