Hydrochloric Acid → ((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-ylmethanone

HRID 77423Notes

Reaction equation

HRID 77423 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])[CH:14]=2)[CH2:9]1)(C)(C)C.Cl.[OH-].[Na+]>CO>[NH2:7][C@H:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:18]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)=[O:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66663930[(S)-6-(pyrrolidine-1-carbonyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester

Product 1

HCID 66664280((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-ylmethanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(S)-6-(pyrrolidine-1-carbonyl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester (0.70 g) in MeOH (5 ml) was added concentrated hydrochloric acid (5 ml). After one hour, the mixture was basified with concentrated sodium hydroxide solution and extracted three times with DCM. The combined organic phases were dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 244.34 (C15H20N2O); MS (ESI): 245 (M+H+).

Workup

  1. extractionextracted three times with DCM
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product was thus obtained with the molecular weight of 244.34 (C15H20N2O)

Sources & evidence

ORD record
ord-c61dc315bc1644b7bee9aed92cbb4817
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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