Hydrochloric Acid → (R)-5-Bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

HRID 1854547Notes

Reaction equation

HRID 1854547 reaction equation
[ClH:1].[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@H:6]([C:17]([O:19]C)=[O:18])[N:7](C(OC)=O)[CH2:8]2.BrC1C=CC=C2C=1C[C@H](C(O)=O)N(C(OC)=O)C2>O>[ClH:1].[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@H:6]([C:17]([OH:19])=[O:18])[NH:7][CH2:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 117720268(R)-5-Bromo-2-(methoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 117722930Dimethyl (3R)-5-bromo-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylate

Product 1

HCID 117720332(R)-5-Bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Add water (1.3 L) and 36.5% hydrochloric acid (9.07 Kg, 90.81 moles) to a mixture of dimethyl (3R)-5-bromo-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylate and (3R)-5-bromo-2-methoxycarbonyl-3,4-dihydro-1H-isoquinoline-3-carboxylic acid (Preparation 3a) (520 g, 1.27 moles) in an appropriate vessel and stir the mixture at 95° C. After 12 hours cool the mixture to 10° C. and stir for 15 minutes. Filter the mixture and dry the solid under vacuum at 40° C. give the title compound (332 g, 1.13 moles). MS (m/z): 256.1 (M-Cl (79Br)), 258 (M-Cl (81Br)).

Workup

  1. temperatureAfter 12 hours cool the mixture to 10° C.
  2. stirringstir for 15 minutes
  3. filtrationFilter the mixture
  4. customdry the solid under vacuum at 40° C.

Sources & evidence

ORD record
ord-acde8c0366e2454fb7fda09301481aee
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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