HCID 86755937, compound → HCID 23289236, compound

HRID 366462Notes

Reaction equation

HRID 366462 reaction equation
C1([Mg]Br)C=CC=CC=1.[C:9]1([C:15]2([NH2:25])[CH2:24][CH2:23][C@H:22]3[C@H:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[C:9]1([C:15]2([NH2:25])[CH2:24][CH2:23][CH:22]3[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)[CH2:16]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 86755937HCID 86755937, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 23289236HCID 23289236, compound

Procedure

This material was prepared from cis/trans-2-tetralone and phenylmagnesium bromide utilizing a procedure analogous to those described in Preparation 89. The crude HCl salt of the amine was purified by preparative C18-RP-HPLC using a 15%→100% CH3CN pH 4.5, 50 mm NH4OAc gradient, followed by concentration in vacuo and extraction of the free-base into Et2OAc from 1N NaOH to obtain a 2:1 mixture of pure trans/cis-2-phenyl-decahydronaphthalen-2-ylamine.

Workup

  1. customthose described in Preparation 89
  2. customThe crude HCl salt of the amine was purified by preparative
  3. concentrationfollowed by concentration in vacuo and extraction of the free-base into Et2OAc from 1N NaOH
  4. customto obtain

Sources & evidence

ORD record
ord-bdc11556dfe6486c8997b0d395774a58
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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