2-Naphthalenecarboxylic acid, 1-hydroxy-, methyl ester → (1S,2S)-2-aminocyclohexanol

HRID 1501886Notes

Reaction equation

HRID 1501886 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[N:8]1CC2C3C=CC=CC=3C(C=O)=CC=2C1=O.C[O:25]C(C1C=CC2C(=CC=CC=2)C=1O)=O>>[NH2:8][C@H:3]1[CH2:4][CH2:5][O:25][CH2:7][C@@H:2]1[OH:1].[NH2:8][C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]1[OH:1]

Participants

4

Reactant 2

HCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 892165982-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde

Product 2

HCID 7057408(1S,2S)-2-aminocyclohexanolHCID 54180780(3R,4S)-4-Aminotetrahydro-2H-pyran-3-ol

Procedure

5-Bromo-8-[(1S,2S)-2-hydrocyclohexyl]-3,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one was prepared employing the procedures described for the construction of 2-[(1S,2S)-2-hydroxycyclohexyl]-3-oxo-2,3-dihydro-1H-benzo[e]isoindole-5-carbaldehyde in Example 1, substituting methyl 8-hydroxyquinoline-7-carboxylate for 1-hydroxy-2-naphthoic acid methyl ester, and substituting provide (3R,4S)-4-aminotetrahydro-2H-pyran-3-ol for (1S,2S)-2-aminocyclohexanol.

Sources & evidence

ORD record
ord-feae68e3e36a40efac717ab4a4d2466e
Source dataset
uspto-grants-2015_12
Patent number
US09206200B2

Reaction notes

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