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

HRID 1913806Notes

Reaction equation

HRID 1913806 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-a9769841319943b8a05cb708a1363c2a
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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