(1R,2S,3R,4R,5R)-2-Amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol → HCID 71258191, compound

HRID 2274315Notes

Reaction equation

HRID 2274315 reaction equation
[NH2:1][C@@H:2]1[C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:6]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:5]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][C@H:3]1[OH:33].N[C@H]1[C@H](OCC2C=CC=CC=2)[C@@H](OCC2C=CC=CC=2)[C@H](COCC2C=CC=CC=2)C[C@H]1O>>[NH2:1][C@H:2]1[C@H:7]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C@@H:6]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:5]([CH2:24][O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:4][C@@H:3]1[OH:33]

Participants

3

Reactant 2

HCID 86727203(1R,2S,3R,4R,5R)-2-Amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanolHCID 86727206HCID 86727206, compound

Product 1

HCID 71258191HCID 71258191, compoundYield 58%

Procedure

The product of step 1 was an enantiomeric isomer of (1R,2S,3R,4R,5R)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol described above in Intermediate Example 3, Step 3. It was prepared via a synthetic sequence substantially identical to that described above for Intermediate Example 3 Steps 1-3, starting from the enantiomeric (1R,2R,3S,4S,5S)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol. The purification conditions for each step reaction were also the same as described, (1S,2R,3S,4S,5S)-2-Amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol was obtained as a white solid with overall yield 58% employing procedures substantially as described for the Intermediate Example 3. 1H NMR (400 MHz, CDCl3) δ 7.37-7.25 (m, 15H), 4.98 (d, J=11.3 Hz, 1H), 4.84 (d, J=10.8 Hz, 1H), 4.69 (d, J=11.3 Hz, 1H), 4.56 (d, J=10.8 Hz, 1H), 4.47 (s, 2H), 3.64 (dd, J=4.9, 8.9 Hz, 1H), 3.54-3.48 (m, 2H), 3.30-3.26 (m, 1H), 3.16 (t, J=9.4 Hz, 1H), 2.52-2.50 (m, 1H), 2.08-2.03 (m, 1H), 1.76-1.72 (m, 1H), 1.58-1.52 (m, 1H).

Workup

  1. customIt was prepared via a synthetic sequence substantially identical to
  2. customThe purification conditions
  3. customfor each step reaction

Sources & evidence

ORD record
ord-5e7570545dda4be29a0044802a5b3144
Source dataset
uspto-grants-2015_09
Patent number
US09126957B2

Reaction notes

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